Hydrochloric Acid → 5-(4-fluorobenzyl)-2H-tetrazole

Temperature

90 °C

To a solution of (4-fluorophenyl)acetonitrile (5.00 g, 37.0 mmol) in 100 mL of toluene was added sodium azide (7.22 g, 111 mmol), triethylamine (15.5 mL, 111 mmol), and concentrated aqueous HCl solution (9.25 mL, 111 mmol). The reaction was heated at 90° C. overnight. The solution was cooled to room temperature and extracted with water and 1N NaOH solution. The combined aqueous layers were washed with ether (3×), acidified with concentrated aqueous HCl solution, and the resulting precipitate was collected by filtration and rinsed with 0.1N HCL solution. The resulting solid was azeotroped from toluene to provide 5-(4-fluorobenzyl)-2H-tetrazole. ESI+MS: 178.9 [M+H]+.

1. temperatureThe solution was cooled to room temperature
2. extractionextracted with water and 1N NaOH solution
3. washThe combined aqueous layers were washed with ether (3×)
4. filtrationthe resulting precipitate was collected by filtration
5. washrinsed with 0.1N HCL solution
6. customThe resulting solid was azeotroped from toluene

ORD record

ord-8d2a129ce5d34b87bbe44383b13606ab

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569589B2